A cityscape at dusk with a prominent dome-shaped building, a waterfront, and a circular structure with multiple towers.

Search Vacation Homes in Madison

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Madison vacation homes

A large, multi-story house with a stone facade, a spacious driveway, and a well-maintained lawn.

1. 3-bedroom pet friendly home in Madison walking distance to beach & winery

3-bedroom pet friendly home in Madison walking distance to beach & winery
Madison-on-the-Lake
10.0 out of 10, Exceptional, (2 reviews)
"The host was responsive and kind. The house was very well equipped, clean and comfortable! 5 stars!"
United States
Stacy S.
The price is ￥23,684
￥38,368 total
includes taxes & fees
Nov 8 - Nov 9
3-bedroom pet friendly home in Madison walking distance to beach & winery
A modern living room with a wooden wall, a sofa, a coffee table, and a dining area with chairs.

2. Highland House | Wine Country | Private Hot Tub

Highland House | Wine Country | Private Hot Tub
Madison
The price is ￥41,738
￥48,436 total
includes taxes & fees
Nov 9 - Nov 10
Highland House | Wine Country | Private Hot Tub
A modern living room with a sofa, chairs, and a coffee table. Large windows offer a view of trees.

3. Ledge House Vintage Retreat | Hot Tub & Fire Pit

Ledge House Vintage Retreat | Hot Tub & Fire Pit
Madison
The price is ￥50,659
￥59,232 total
includes taxes & fees
Nov 17 - Nov 18
Ledge House Vintage Retreat | Hot Tub & Fire Pit
A modern kitchen with blue cabinets, a stainless steel dishwasher, a gas stove, and a microwave.

4. Dog-Friendly Retreat Near Wineries/Spire/GOTL

Dog-Friendly Retreat Near Wineries/Spire/GOTL
Madison-on-the-Lake
9.6 out of 10, Exceptional, (39 reviews)
"Amazing stay clean and safe ."
United States
TerriAnn M.
The price is ￥30,410
￥48,001 total
includes taxes & fees
Nov 5 - Nov 6
Dog-Friendly Retreat Near Wineries/Spire/GOTL
A backyard patio with a table and chairs, a grill, and a barbecue smoker.

5. Charming 2-bedroom house in delightful Madison with AC

Charming 2-bedroom house in delightful Madison with AC
Madison-on-the-Lake
8.0 out of 10, Very good, (5 reviews)
"Beautiful, pet friendly , host was easy to communicate with , we would stay again"
United States
Robin T.
The price is ￥42,630
￥47,998 total
includes taxes & fees
Nov 6 - Nov 7
Charming 2-bedroom house in delightful Madison with AC
A cozy living room with a leather sofa, a wooden coffee table, and a large window offering a view of the outdoors.

6. Lakeside Chalet | Private Lake | Hot Tub | Views

Lakeside Chalet | Private Lake | Hot Tub | Views
Madison
Lakeside Chalet | Private Lake | Hot Tub | Views
A stone fire pit with burning logs, surrounded by a grassy area and two wooden chairs.

7. Center Strip | Pets OK | Wi-Fi | Near Wineries

Center Strip | Pets OK | Wi-Fi | Near Wineries
Geneva
9.4 out of 10, Exceptional, (259 reviews)
"We enjoyed our stay. Place was as described and conveniently located in walking distance of a lot of the strip. Very clean with good air conditioning."
United States
Patrick G.
The price is ￥8,901
￥27,490 total
includes taxes & fees
Nov 8 - Nov 9
Center Strip | Pets OK | Wi-Fi | Near Wineries
A bedroom with a bed, a ceiling fan, a TV on a dresser, and two windows with blinds.

8. A great stay, close to Spire, GOTL, & Wineries....King Bed!

A great stay, close to Spire, GOTL, & Wineries....King Bed!
Geneva
10.0 out of 10, Exceptional, (49 reviews)
"Very clean.. spacious, Close to wineries."
United States
frances f.
The price is ￥15,120
￥30,018 total
includes taxes & fees
Nov 16 - Nov 17
A great stay, close to Spire, GOTL, & Wineries....King Bed!
A living room with a brown sofa, a coffee table, a TV, and a ceiling fan.

9. A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!

A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Geneva
10.0 out of 10, Exceptional, (24 reviews)
"The accommodations were exactly what we were looking for…everything we needed in a comfortable and cozy spot."
United States
Daniel K.
The price is ￥14,977
￥30,984 total
includes taxes & fees
Nov 8 - Nov 9
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
A square fire pit table with two metal chairs on a wooden deck.

10. Beautiful cabin situated on wooded land with nice yard clearing and small stream

Beautiful cabin situated on wooded land with nice yard clearing and small stream
Madison
9.8 out of 10, Exceptional, (14 reviews)
"Wonderful stay :) "
United States
Jennifer S.
The price is ￥20,526
￥25,405 total
includes taxes & fees
Nov 14 - Nov 15
Beautiful cabin situated on wooded land with nice yard clearing and small stream
A bedroom with a bed, a ceiling fan, a window with patterned curtains, and a door.

11. Quaint cottage a short walk from the GTOL strip!

Quaint cottage a short walk from the GTOL strip!
Geneva-on-the-Lake
9.6 out of 10, Exceptional, (93 reviews)
"Clean, great location, plenty of space for two people, arcade was a nice touch!"
United States
Rita D.
The price is ￥14,921
￥28,342 total
includes taxes & fees
Nov 17 - Nov 18
Quaint cottage a short walk from the GTOL strip!
A covered outdoor deck with a black wicker sofa, a small table, and a chair.

12. On The Strip • Cozy GOTL Vacation Cottage

On The Strip • Cozy GOTL Vacation Cottage
Geneva
9.4 out of 10, Exceptional, (112 reviews)
"Very pleasant stay"
United States
Daniel M.
The price is ￥11,868
￥38,810 total
includes taxes & fees
Nov 8 - Nov 9
On The Strip • Cozy GOTL Vacation Cottage
Living area

13. Spacious 2bed on a Private 1 acre Lot by Lake, Sleeps 8--Walk to Strip & Golf

Spacious 2bed on a Private 1 acre Lot by Lake, Sleeps 8--Walk to Strip & Golf
Geneva
9.0 out of 10, Wonderful, (59 reviews)
"Great location. Walkable to town. Very clean home and very comfortable. Great backyard and front and back decks. Great amenities"
United States
Susanne
The price is ￥12,124
￥34,788 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 2bed on a Private 1 acre Lot by Lake, Sleeps 8--Walk to Strip & Golf
A modern living room with a sofa, armchairs, a coffee table, and a dining area with a table and chairs.

14. Hot Tub, Fire Pit, Private Backyard - Near Wineries & SPIRE

Hot Tub, Fire Pit, Private Backyard - Near Wineries & SPIRE
Geneva
9.8 out of 10, Exceptional, (29 reviews)
"Amazing stay! Host was super responsive, property had all the amenities amd was located in a good area."
United States
Jamie L.
The price is ￥28,370
￥59,009 total
includes taxes & fees
Nov 9 - Nov 10
Hot Tub, Fire Pit, Private Backyard - Near Wineries & SPIRE
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

15. Wine Country Escape - Hot Tub - Sleeps 12

Wine Country Escape - Hot Tub - Sleeps 12
Geneva
10.0 out of 10, Exceptional, (15 reviews)
"Great place to stay! Everything was wonderful, including host!"
United States
caryn l.
The price is ￥27,631
￥83,745 total
includes taxes & fees
Nov 10 - Nov 11
Wine Country Escape - Hot Tub - Sleeps 12
An outdoor deck with a wooden table and wicker chairs, a grill, and a view of greenery.

16. Dog-friendly 2BR with fireplace, 7 miles to SPIRE and minutes from the wineries.

Dog-friendly 2BR with fireplace, 7 miles to SPIRE and minutes from the wineries.
Geneva-on-the-Lake
9.0 out of 10, Wonderful, (6 reviews)
"Adorable and host thought of everything. "
United States
Kimberly M.
The price is ￥17,663
￥38,219 total
includes taxes & fees
Nov 30 - Dec 1
Dog-friendly 2BR with fireplace, 7 miles to SPIRE and minutes from the wineries.
A living room with a sofa, a coffee table, and a door.

17. GOTL Hideaway Hut- Sunset Vacation Rentals

GOTL Hideaway Hut- Sunset Vacation Rentals
Geneva
9.4 out of 10, Exceptional, (75 reviews)
"We always enjoy our stay in Geneva and using sunset! The fenced in backyard was great for our dog!"
United States
Shelby B.
The price is ￥21,044
￥41,232 total
includes taxes & fees
Nov 5 - Nov 6
GOTL Hideaway Hut- Sunset Vacation Rentals
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a backsplash made of rectangular stone tiles.

18. GOTL Coastal Cottage- Sunset Vacation Rentals

GOTL Coastal Cottage- Sunset Vacation Rentals
Geneva
9.0 out of 10, Wonderful, (88 reviews)
"location"
United States
Donna T.
The price is ￥21,044
￥41,232 total
includes taxes & fees
Nov 17 - Nov 18
GOTL Coastal Cottage- Sunset Vacation Rentals
A living room with a dark grey sofa, white armchair, and a coffee table with a vase of flowers. There are three framed artworks above the sofa and a plant on the side.

19. Stylish 4 Bedroom Home in Geneva, Ohio. Near Wineries, SPIRE Institute, GOTL

Stylish 4 Bedroom Home in Geneva, Ohio. Near Wineries, SPIRE Institute, GOTL
Geneva
10.0 out of 10, Exceptional, (17 reviews)
"Great place and close to lots of places and activities."
United States
Lawrence F.
Stylish 4 Bedroom Home in Geneva, Ohio. Near Wineries, SPIRE Institute, GOTL
A modern kitchen with stainless steel appliances, a wooden dining table, and a bench.

20. GOTL Retreat, short walk to strip, 15 min to Spire

GOTL Retreat, short walk to strip, 15 min to Spire
Geneva on the Lake
9.2 out of 10, Wonderful, (9 reviews)
"location was great. Loved the outside seating area."
United States
Kim
The price is ￥20,526
￥52,088 total
includes taxes & fees
Nov 17 - Nov 18
GOTL Retreat, short walk to strip, 15 min to Spire
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison Hotel Reviews

SkyLight Inn Cleveland - Willoughby

SkyLight Inn Cleveland - Willoughby

10/10 Excellent
"😁"
Carmen 2-night trip
Posted 18 hours ago
SkyLight Inn Cleveland - Willoughby

Find out more about Madison

Madison Vacation Homes information

Number of reviews
790
Accommodation
226 Vacation Homes
Lowest Price
￥25,405
Highest Price
￥83,745